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Search results; Over 1,000 homes in Dalton

Top guest favourite
Home in Dalton
Brooksong, the perfect Berkshires getaway
5 bedrooms, 7 beds, 2.5 private bathrooms
9–14 Sept
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4.93 out of 5 average rating, 211 reviews
Top guest favourite
Farm stay in Dalton
Gorgeous Working Farm in the Berkshires
5 bedrooms, 9 beds, 3 bathrooms
4–9 Sept
5.0 out of 5 average rating, 20 reviews
Guest favourite
Room in Dalton
Mother in Law unit in Dalton
1 king bed, 1 bathroom
7–12 Sept
4.93 out of 5 average rating, 174 reviews
Top guest favourite
Guest suite in Dalton
Berkshires getaway: nature, culture & relaxation
1 bed, 1 bathroom
8–13 Sept
4.99 out of 5 average rating, 80 reviews
Guest favourite
Home in Dalton
Willowbrook: A Sun Filled, Mid-century Modern Home
7 bedrooms, 8 beds, 4.5 bathrooms
20–25 Sept
4.78 out of 5 average rating, 113 reviews
Guest favourite
Flat in Dalton
1843 House - Bright and Airy 5 Rooms (2 Bedrooms)
2 bedrooms, 3 beds, 1 bathroom
31 Oct – 5 Nov
4.9 out of 5 average rating, 21 reviews
Top guest favourite
Home in Lanesborough
Tranquil mid-century modern Berkshires retreat
3 bedrooms, 4 beds, 2.5 bathrooms
7–12 Sept
4.99 out of 5 average rating, 135 reviews
Top guest favourite
Home in Pittsfield
Lakefront home in the heart of the Berkshires
4 bedrooms, 6 beds, 4 bathrooms
6–11 Sept
4.94 out of 5 average rating, 47 reviews
Guest favourite
Home in Pittsfield
Berkshire Views
6 bedrooms, 7 beds, 4 bathrooms
13–18 Sept
5.0 out of 5 average rating, 19 reviews
Top guest favourite
Home in Hinsdale
Berkshire Lake-side Retreat
2 bedrooms, 4 beds, 2 bathrooms
7–12 Sept
5.0 out of 5 average rating, 17 reviews
Guest favourite
Cabin in Hinsdale
Relaxing Berkshire cabin on Lake Ashmere
2 bedrooms, 3 beds, 1 bathroom
4–9 Sept
4.96 out of 5 average rating, 50 reviews
Top guest favourite
Home in Pittsfield
Charming Historic Retreat, <15 min from Lenox
4 bedrooms, 6 beds, 2.5 bathrooms
11–16 Sept
5.0 out of 5 average rating, 15 reviews
Top guest favourite
Home in Pittsfield
Solomon Ely Homestead set in walkable downtown
4 bedrooms, 4 beds, 1.5 bathrooms
8–13 Sept
5.0 out of 5 average rating, 45 reviews
Top guest favourite
Flat in Pittsfield
Downtown Apartment A
2 bedrooms, 3 beds, 1 bathroom
28 Sept – 3 Oct
4.93 out of 5 average rating, 116 reviews
Guest favourite
Home in Pittsfield
Beautiful Lake-view Getaway!
2 bedrooms, 2 queen beds, 1 bathroom
9–14 Sept
4.97 out of 5 average rating, 75 reviews
Guest favourite
Home in Dalton
Cleveland House - renovated Berkshires' gem.
6 bedrooms, 8 beds, 3 bathrooms
1–6 Aug
4.99 out of 5 average rating, 181 reviews
Guest favourite
Home in Pittsfield
The Reel Retreat | Theatre & Firepit • Game Room
4 bedrooms, 4 beds, 2 bathrooms
21–26 Sept
5.0 out of 5 average rating, 17 reviews
Guest favourite
Home in Pittsfield
Net Zero home with rustic Berkshire charm
3 bedrooms, 4 beds, 1 bathroom
28 Oct – 2 Nov
4.93 out of 5 average rating, 134 reviews
Guest favourite
Home in Lanesborough
Cozy Cottage in Berkshires: Minutes to Jiminy Peak
4 bedrooms, 5 beds, 1.5 bathrooms
6–11 Sept
4.97 out of 5 average rating, 78 reviews